By Eric Berman, REALTOR® | The Eric Berman Team at Compass
TL;DR:
Housing is meaningfully cheaper and the cultural offering is a genuine draw. What most comparisons understate is property taxes — Illinois carries among the highest effective rates in the country, and in Cook County the assessment system works differently enough from Nassau's that it needs learning rather than assuming. The reassuring part: Illinois transactions involve attorneys, which makes the process closer to New York's than most relocation destinations. And on the seller side, the Long Island sale sets the budget and should be settled before anything in Chicago gets serious.
Start With the Long Island Sale
The transaction that governs the move happens here — it sets the budget, the timeline, and whether the household moves on its own schedule.
Before touring anything in Chicago, a seller should know what the current home nets: commission, New York State Transfer Tax at four dollars per thousand, attorney fees generally $1,500 to $3,500, preparation, and carrying costs for a longer listing period than hoped. The full breakdown of what a Long Island sale costs covers each line.
A seller who establishes Illinois residency before the Long Island closing becomes a New York nonresident for that transaction, triggering Form IT-2663 — an estimated payment at closing of 8.82 percent of net gain. It's a prepayment rather than an additional tax, refundable where the real figure comes in lower, but it reduces the wire.
For a long-held home, capital gains deserve attention: the exclusion covers $250,000 single and $500,000 filing jointly, and improvement records reduce the taxable figure substantially. The full treatment of how gain is calculated covers the mechanics.
The Process Will Feel Familiar
This is genuinely good news for a New York seller and the original mentioned it in a clause.
Illinois residential transactions typically involve attorneys on both sides. The standard practice includes an attorney review period after contract signing, during which counsel can propose modifications or, in some circumstances, terminate — a structural feature New York doesn't have but that will feel more recognizable than a title-company closing.
Compare that to Texas, Georgia, or Florida, where a New York buyer would find no attorney representing them at the table. In Illinois, having counsel is the norm rather than an arrangement you have to construct.
Two attorneys are needed rather than one, since licensing is state-specific. A New York attorney who handles relocations can often refer. The fuller picture of what the attorney handles on the New York side describes the role that carries over.
Illinois also imposes transfer taxes at state, county, and in Chicago, municipal levels, with the allocation between buyer and seller varying. Confirm the specifics for a given municipality with local counsel.
Property Taxes Need More Attention Than the Headline
The affordability case is real on housing prices. On property taxes it's more complicated, and this is the sixth thing most relocation content gets partly wrong.
Illinois carries among the highest effective property tax rates in the country. A household comparing Nassau County's bill to an Illinois bill on a much less expensive home may find the gap narrower than the price difference suggests — and in some collar county communities, comparable.
Cook County's system is distinctive and worth learning rather than assuming. Assessments are conducted on a triennial cycle by township, and the county operates a well-used appeal process through the Assessor's office and the Board of Review, with defined filing windows. A meaningful share of owners appeal, and successful appeals reduce the bill.
For someone arriving from Nassau County — where grievance filing is also a live practice — the concept will be familiar even though the mechanics differ. What matters practically:
Ask about the assessment cycle and appeal windows for any property under consideration, since a recent reassessment may not yet be reflected in the bill a seller quotes.
Homeowner exemptions require application rather than transferring automatically. Illinois offers a general homestead exemption and additional exemptions for qualifying owners, all administered locally.
Collar counties differ from Cook. DuPage, Lake, Will, and Kane operate their own systems with their own rates, and the difference between two similarly priced homes across a county line can be substantial.
Pull the actual current tax bill on any specific property. Rates, exemption amounts, and appeal deadlines change, so confirm with the relevant county assessor and a local professional.
City or Suburbs, on Measurable Terms
The decision that most shapes the move, and it turns on things that can be checked.
Transit access. Chicago's rail and bus network makes car-free living genuinely practical in much of the city — a real difference from Long Island, where LIRR access is a commuting solution rather than a substitute for a car. Commuter rail serves the suburbs, and coverage varies considerably by line and by station distance.
Housing stock. The city runs to condominiums, two- and three-flats, and historic single-family construction on smaller lots. Suburban areas offer more square footage and land per dollar. Condominium purchases bring association dues and reserve considerations that a Long Island single-family seller may not have dealt with.
County lines matter because of the tax differences above, and services are county-administered.
Winter is a genuine adjustment. Longer, colder, and snowier than Long Island's, with heating costs and maintenance implications worth budgeting rather than absorbing as a surprise.
The reliable sequence: identify where the work is, test the commute at the hour it would actually happen, pull tax bills on specific properties, and check assessment and appeal history before offering.
Practical Logistics
Roughly 800 miles — a genuine long-distance relocation. Interstate movers should be booked well ahead, with vehicle transport often cheaper than driving.
On sequencing: selling the Long Island home first produces clean funds, a defined budget, and a purchase offer with no contingency on another sale, which matters at this distance. The trade-off is potentially needing temporary housing. Buying first means carrying both properties, frequently $12,000 to $16,000 monthly combined at Long Island price points.
Worth noting on the Illinois side: the attorney review period in a standard contract means the transaction has a defined early window in which terms can still move. A buyer should understand what that period allows before signing rather than after.
A Worked Example
Consider a composite case — a Nassau County household relocating for a Chicago-area position, selling a colonial that comped near $1,060,000.
Two things changed their approach. Their Illinois attorney explained the assessment and appeal system, and they discovered that one property they liked had been reassessed recently with the increase not yet reflected in the bill the listing showed. The actual figure going forward was materially higher.
Second, they compared a Cook County property against one in a collar county at a similar price. The tax difference was substantial and appeared in neither listing — they found it by pulling both bills.
On the New York side, they sold first. Their attorney's early title review turned up a 2011 permit never closed out, resolved in six weeks before listing. They closed in May, spent six weeks in a rental, and bought with cash in hand and no sale contingency.
Where to Start
Build the net-proceeds model on the Long Island home before touring anything. Call the town or village building department about permits. Engage a New York real estate attorney early and ask for an Illinois referral. Talk to a CPA about IT-2663 and capital gains before setting a closing date.
On the Illinois side: pull the actual current tax bill for any specific property, ask about the assessment cycle and whether a recent reassessment is reflected, and ask about appeal history and windows. Confirm which exemptions apply and what applying requires. Compare across county lines deliberately. And test the commute at the hour it would actually happen.
Sellers wanting a current read on where their Long Island home sits can start with a quiet look at present value, and more market and process coverage lives in Local Insights.
The Honest Bottom Line
Chicago is more affordable than Long Island on housing and offers transit access that makes car-free living genuinely workable — both real advantages.
What deserves more scrutiny is the tax picture. Illinois rates are among the highest in the country, the assessment and appeal system in Cook County works differently enough from Nassau's that it has to be learned, and the difference between two similarly priced homes across a county line can be substantial. None of that appears in a listing.
The reassuring part is procedural: Illinois transactions involve attorneys, so a New York seller won't find themselves at a closing table with nobody on their side. For anyone working through what their Long Island home would net before any of the Chicago decisions get made, that conversation is available whenever the timing suits.
This is general information, not legal, tax, or financial advice. Illinois property tax rates, assessment cycles, exemption criteria, appeal deadlines, and transfer taxes vary by county and municipality and change over time. Confirm current specifics with an Illinois attorney and the relevant county assessor, and confirm New York specifics with a licensed New York real estate attorney and a CPA.
FAQs
Are property taxes lower in Illinois than on Long Island?
Less than the housing price difference suggests. Illinois carries among the highest effective property tax rates in the country, so a household comparing a Nassau County bill to an Illinois bill on a much less expensive home may find the gap narrower than expected — and in some collar county communities, comparable. Cook County and the collar counties operate different systems with different rates. Pull the actual current bill on any specific property rather than relying on averages, and ask whether a recent reassessment is reflected in it.
Does Illinois require an attorney to buy a home?
Illinois residential transactions typically involve attorneys on both sides, including an attorney review period after contract signing during which counsel can propose modifications or, in some circumstances, terminate. For a New York seller that's genuinely reassuring — the process is closer to New York's than to Texas, Georgia, or Florida, where a buyer would find no attorney representing them at closing. Two attorneys are needed since licensing is state-specific, and a New York attorney who handles relocations can often refer.
How does the Cook County assessment appeal process work?
Assessments are conducted on a triennial cycle by township, and the county operates an appeal process through the Assessor's office and the Board of Review with defined filing windows. A meaningful share of owners appeal, and successful appeals reduce the bill. For someone arriving from Nassau County, where grievance filing is also a live practice, the concept will be familiar even though the mechanics differ. Ask about the assessment cycle, the appeal window, and any appeal history for a specific property before offering.
What is Form IT-2663 and does it apply to this move?
It applies if the Long Island home sells after the seller has established Illinois residency. New York requires nonresident sellers to make an estimated payment at closing of 8.82 percent of net gain, filed through Form IT-2663. It isn't an additional tax — it's a prepayment against actual New York State income tax liability, refunded when the return is filed if the real number comes in lower. Practically, it reduces the amount wired at closing, which catches sellers who have already committed those proceeds to a purchase.
Should I sell my Long Island home before buying in Chicago?
Generally yes at 800 miles. Selling first produces clean funds, a defined budget, and a purchase offer with no contingency on another sale, which matters when coordinating simultaneous closings across that distance is difficult. The trade-off is potentially needing temporary housing. Buying first means carrying both properties, frequently $12,000 to $16,000 monthly combined at Long Island price points, which pressures the sale toward accepting less than the home would otherwise bring.
By Eric Berman, REALTOR® | The Eric Berman Team at Compass
Eric Berman | Long Island & Queens Associate Broker | Compass
1468 Northern Blvd, Manhasset, NY 11030
(917) 225-8596 | eric@ericbermanre.com | theericbermanteam.com
